Working for Trump-like bosses

I worked at a legendary publisher where the CEO was a raging alcoholic. He was so bad, a noted snark magazine did a take-out on him. He once actually swung from a chandelier during a big trade dinner at the Downtown Athletic Club, and occasionally would order a janitor to follow him through the newsroom while he swept files, papers and anything else he found atop cabinets onto the floor. I witnessed that. He got married and dried out. One day a reporter brought his young children to the office and ran into the CEO. The CEO said sternly, "Follow me," led them to his office. He rummaged in a closet, then handed the kids two boxes of golf balls.

I don't know if he was Trump-like, but the Publisher at my last stop (before the hedge fund took over) had apparently bought the world's last remaining ream of paper with the printer holes down the side, and if you made an error in the paper, you might come in the next day to find a dot matrix-printed note and a clipping of the error (circled in red) taped to your desk.

He also really, really, really focused on the difference between an en dash, an em dash, and a hyphen.

I also worked for a publisher nicknamed The Beast, who would impulsively blame and yell at staff for assorted minor infractions -- like using more than one paper towel per bathroom visit, claim he could put out the mag better by himself, and piss and moan that he never got the recognition he deserved, like the Sulzburgers, Newhouses, or Ridders.

The only issue I had with a publisher was working out as the same gym as him. He was an old dude and old school so locker room nudity was nothing to him. Nothing like being questioned on a story while someone’s balls are dangling next to you.

When I was a broke grad student living in an SEC town, I got a job helping out at my apartment complex. The job entitled me to half-off of my rent every month. I worked for the property manager at the biggest apartment complex in town, even though he had no experience in property management prior to taking this job. His old man was a pretty wealthy, well-connected guy and got him the job.

Anyway, the manager, Neal, would constantly ask me if I had seen the Bill O'Reilly Show from the night before (this was circa 2004). I always told him I hadn't, which was the truth. He never seemed to remember that I just never watched that show or any other on FNC. When Neal wasn't asking me about O'Reilly he was always complaining about certain groups of renters or potential renters that always seemed to have the same physical characteristics.

Aside from that troubling behavior, Neal would always talk about how awesome and well-run our biggest competitor was and how we should run some sort of joint cross-promotion event even though they were owned by a completely different company.

After I graduated I learned that Neal was renting out apartments all over the property to local gangsters as a way to launder money.

Worked for a guy at my last stop who was both lazy and a micromanager. Everything had to go through him from paying of bills to layouts to you name it. The problem was he would take forever to do anything so bills were paid late, pages were proofed after they needed to go to the printer, hiring of vacant positions dragged, firing of dipshits dragged. It was awful. We all got lovely notes from our health care provider that our coverage had lapsed because the dude didn't pay the bill. We had the money taken from our paychecks, mind you, but the guy didn't pay his end. The cheap SOB often would just combine jobs so he wouldn't have to pay the extra salary. Yes most papers are going that route, but he tried to tell us this was best for us to be doing the work of four people because we got a 1 to 2 percent salary bump. He was also egotistical as fuck. When I finally left, I wrote a farewell column thanking the people who got me started in my career and were influential in helping me along the way. I left him out because he was just my boss. He didn't hire me or give me any big breaks to help advance my career. Still, I got a phone call from him extolling how I left certain people out and how grateful I should have been that he (and he alone) was able to keep the paper going so I wouldn't be out of a job. It was honestly miserable to work for him and I didn't even face the worst of it. There were others at the paper who had to put up with hostile work environments because of him or because he wouldn't do anything to stop it, yet we all had to kiss his ass.

Final note about him, dude was married and had one or two kids when his wife got pregnant and had their daughter. Within six months, he left her with their baby for some Brazilian woman who was considerably younger.

Final note about him, dude was married and had one or two kids when his wife got pregnant and had their daughter. Within six months, he left her with their baby for some Brazilian woman who was considerably younger.

Small-town publisher was an alcoholic, and kept getting pulled over for DUI (but never charged with anything). Finally had to make a deal with the sheriff that he would only go to the bar nearest to his house and would drive his riding lawnmower to and from.
Same bar turned into an illegal after-hours strip club after closing time, and that's where the publisher met his wife, who we had covered as a high school athlete and who was 19 at the time.